Specific 1-hydrocarbyloxy 2,2,6,6-tetramethylpiperidine derivatives bearing a reactive functional group have been described in end-use applications other than polymer stabilization. For example, 1-benzyloxy-4-hydroxy-2,2,6,6-tetramethylpiperidine has been detected during the photolysis of 4-hydroxy-1-oxyl-2,2,6,6-tetramethylpiperidine in toluene (J. F. W. Keana, J. Org. Chem., 36, 209 (1971). A salt of 1-[1-(2-cyano-2-propyl)oxy-2,2,6,6-tetramethylpiperidin-4-yl]-amino-3-(2-n itro-1-imidazolyl)-2-prop anol has been used in a study of nitroxyl radiosensitizers (B. C. Millar et al., Radiat. Res., 88, 369 (1988).
U.S. Pat. Nos. 4,619,956; 4,426,471; 4,426,472; 4,344,876 and 4,234,728 include hindered amine substituted N-(hydroxyalkyl)amino and N-(alkoxymethyl)amino substituted s-triazine derivatives. However, none of these patents teaches the use of 1-hydrocarbyloxy substituted hindered amines as polymer stabilizers.
U.S. Pat. No. 4,740,544 claims, but does not exemplify bisphenol A bridged N-(hydroxyalkyl)amino-N-(1-alkoxy-2,2,6,6-tetramethylpiperidin-4-yl)-1,3,5 -triazine compounds as polymer stabilizers. This patent does not teach any advantages of using 1-hydrocarbyloxy substituted hindered amine polymer stabilizers.
The use of reactable stabilizers in certain polymer substrates has been described. For example, U.S. Pat. Nos. 4,145,512 and 4,178,279 describe the stabilization of urethanes by molecules which contain combinations of hindered amines and amino, hydroxy or hydrazide groups. The stabilizer molecules are introduced into the prepolymer solution. Aminooxamide hindered amine derivatives have been reacted with acrylic polyols containing anhydride groups (P. A. Callais et al., Proc. Water-Borne High-Solids Coat. Symp., 16, 486 (1989). The use of hydroxy substituted 4-oxamido hindered amine derivatives is taught in U.S. Pat. No. 4,730,017. The use of 1-hydrocarbyloxy substituted hindered amines as polymer stabilizers is not disclosed in these patents.
U.S. Pat. No. 4,910,238 discloses several s-triazine derivatives containing a bis(2-hydroxyethyl)amino or a 2-hydroxyethylamino substituent. There is no overlap between the instant compounds and those of this patent.
The advantages of the reduced basicity of 1-hydrocarbyloxy substituted hindered amines as polymer stabilizers in acid sensitive polymer substrates is first described in copending U.S. patent application Ser. No. 749,470. N-Hydrocarbyloxy derivatives of hindered amine substituted s-triazines are disclosed in copending U.S. patent applications Ser. Nos. 749,470 and 727,340; and U.S. Pat. No. 5,019,613. None of these applications and patent includes compounds with reactive functional groups.
Copending U.S. patent application Ser. No. 480,173 describes the use of non-migrating 1-hydrocarbyloxy hindered amine derivatives as polymer stabilizers. However, the compounds disclosed in application Ser. No. 480,173 differ substantially from the s-triazine derivatives described in the instant invention.